Blends of cyclic vinyl ether containing compounds and epoxides

Claim 2

A composition suitable for photocopolymerization comprising a cyclic vinyl ether containing compound and an epoxy containing compound.

Claim 3

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is selected from the following: The groups Z and Z' represent an dependently hydrogen or an alkyl group having from 1 to 10 carbon atoms; X and X I are members of the class consisting of a bivalent saturated hydrocarbon group, R, having the structure, -C n H 2n -, wherein n is an integer having a value of from 1 to 10; an oxy radical, -O-; and a carbonyl group, -C(O)-; and, in addition X' may be a carbonyloxy group, -O(O)C-, the carbon atom of which is bonded to the 2-position of the dihydropyranyl ring; X and X' may be the same or different provided that taken together they contain either zero or 2 oxygen atoms; a has a value of from zero to 1, a being zero only when X' is the aforesaid carbonyloxy group; Q is a member of the class consisting of the aforesaid R group; a dioxylakylene group, -ORO-, wherein R is as defined above; a dicarboxylate group, -OC-(O)-R'-C(O)O,- wherein R' is the nucleus of a dicarboxylic acid; and a polycarbamate group such as the dicarbamate group, -∝(O)NH-R"-NH-C(O)O-, wherein R", as illustrated, is the nucleus of a diisocyanate; and X, X' and Q taken together is such that the linking chain, -X-Q-X'-, contains an even number of oxygen atoms from two to four, provided that when X and X' are both oxy radicals, the linking chain contains no other oxygen atoms (that is, Q or R), and when X and X' are both carbonyl groups, the linking chain contains four oxygen atoms (that is, Q is -ORO-).

Claim 4

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is 3,4-dihydro-2H-pyran-2-methyl(3,4-dihydro-2H-pyran-2-carboxylates) having the formula: wherein Z and Z' are as above-defined. Preferably a total of from 5 to 7 of the respective Z and Z' groups are hydrogen and correspondingly, from 3 to zero are alkyl groups.

Claim 5

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is alkanedioxy-bis(3',4'-dihydro-2'H-pyran-2'-carbonyl) compounds having the structure: wherein Z ana Z' are as defined in claim 2, and n is an integer from 1 to 10

Claim 6

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihyro-2'H-pyran-2'-oxy)alxanes having the formula: wherein Z, Z' are as defined in claim 2 and n is as defined in claim 4.

Claim 7

A composition as aefined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihydro-2'H-pyran-2'-alkoxy) alkanes having the formula: wherein Z, Z' are as defined in claim 2 and n is as defined in claim 4.

Claim 8

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is bis-(3',4'-dihydro-2'H-pyran-2'-alkyl) carboxylates having the general formula: wherein Z, Z' are as defined in claim 2, n is as defined in claim 4 and R' is the nucleus of a dicarboxylic acid and may be a bivalent aliphatic, cycloaliphatic or aromatic nucleus including corresponding halogen-substituted nuclei.

Claim 9

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound has the general formula: wherein Z, Z' are as defined in claim 2, n is as defined in claim 4, R" is an aliphatic, cyloaliphatie or aromatic radical which may be unsubstituted hydrocarbyl groups or hydrocarbyl groups substituted with halogen or alkoxy groups.

Claim 10

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is selected from one or more of the following: wherein R 1 is hydrogen or methyl, R 1 "' is alkyl of 1 to 10 carbon atoms, and X is selected from wherein n has a value of from 1 to 50 and wherein R 1 ' is the residue of a carboxylic acid and can be (1) hydrogen, (2) alkyl which is substituted with any substituent which does not unduly interfere with the polymerization, or unsubstituted, linear or branched, containing up to 20 carbon atoms, and (3) aryl which is substituted with any substituent which does not unduly interfere with the polymerization or, which is unsubstituted, having 6 to 10 ring carbon atoms; R 3 is hydrogen, alkyl, alkoxy, aryl, cycloalkyl, alkaryl or an aralkyl group having up to 12 carbon atoms and at least (2x-3) of the R 3 groups are hydrogen atoms, and x has a value of 2 to 12.

Claim 11

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is an alkylene oxide adduct of 3,4-dihydropyran-2- methanol of the general formula: wherein R 1 and n are as defined in claim 9.

Claim 12

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound i: of the formula: wherein R 1 , n, R 3 and x are as defined in claim 9.

Claim 13

A composition as defined in claim 1 wherein the cyclic viny ether containing compound is of the formula: wherein R 1 and R 1 ' are as defined in claim 9.

Claim 14

A composition as defined in claim 1 wherein the cyclic viny ether containing compound is of the general formula: wherein R 3 is as defined in claim 9 and R 1 and n are as defined in claim 10.

Claim 15

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula: wherein R 1 , R 3 , n, and x are as defined in claim 9.

Claim 16

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is the reaction product of the following: wherein R 1 , is as defined in claim 9, and pentaerythritol or an aldehyde.

Claim 17

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula:

Claim 18

A composition as defined in claim 1 wherein the cyclic vinyl ether containing compound is of the formula:

Claim 19

A composition as defined in one or more of the claims 1-17 wherein the epoxide is a cycloaliphatic epoxide.

Claim 20

A composition as in claim 18 wherein the cycloaliphatic epoxide has the formula: wherein R 4 through R 21 , which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive; R is a valence bond or a divalent hydrocarbon radical generally containing one to twenty carbon atams inclusive.

Claim 21

A composition as in claim 18 wherein the cycloaliphatic epoxide has the formula: wherein R 1 through R 18 , which can be the same or different are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive.

Claim 22

A composition as in claim 18 wherein the cycloaliphatic epoxide has the formula: wherein the R' are the same or different and are monovalent substituents or monovalent hydrocarbon radicals.

Claim 23

A composition as in claim 18 wherein the cycloaliphatic epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate / bis{3,4-epoxycyclohexylmethyl)-adipate,2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)-cyclohexane-meta-dioxane, vinylcyclohexene diepoxide, a mixture of bis(3,4-epoxycyclohexylmethyl) adipate and 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)-cyclohexane-metadioxane or a mixture of 3,4-epoxy-cyclohexylmethyl-3,4-epoxycyclohexane carboxylate and bis(3,4-epoxycyclohexylmethyl) adipate, preferably including 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxy) cyclohexane-meta-dioxane.

Claim 24

A canposition as defined in one or more of the claims 18-22 which contains minor amounts of one or more glycidyl type epoxides, aliphatic epoxides, epoxy cresol novolac resins, epoxy phenol novolac resins, polynuclear phenol-glycidyl ether-derived resins aromatic and heterocyclic glycidyl amine resins or hydantoin epoxy resins.

Claim 25

A composition as in one or more of the claims 1 - 17 wherein the epoxide is a glycidyl type epoxide.

Claim 26

A composition as in claim 24 which contains a cycloaliphatic epoxide.

Claim 27

A composition as defined in one or more of the claims 1 - 25 which contains a photoinitiator, e.g. any one which is selected from diazonium salts or onium salts, or mixtures thereof.

Claim 28

A composition as defined in one or more of the claims 1 - 26 which contains a substituted or unsubstituted cycloaliphatic monoepoxide, e.g. any substituted one which contains substituents selected from alkyl of 1 to 9 carbon atoms, halogen, oxygen, ether, hydroxyl, ester or a vinyl radical.

Claim 29

. A composition as defined in claim 27 wherein the substituted cycloaliphatic monoepoxide is vinyl substituted cycloaliphatic monoepoxide.

Claim 30

A composition as defined in claim 28 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:

Claim 31

A composition as defined in claim 28 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:

Claim 32

A composition as defined in claim 28 wherein the vinyl cycloaliphatic monoepoxide is of the following formula:

Claim 33

A composition as defined in claim 27 wherein the substituted cycloaliphatic monoepoxide is hydroxyl substituted, e.g. any one which is of the following formula:

Claim 34

A composition as defined in claim 27 wherein the unsubstituted cycloaliphatic monoepoxide is cyclohexene monoepoxide.

Claim 35

A composition suitable for photocopolymerization comprising: (a) a cyclic vinyl ether containing compound, and (b) a vinyl cycloaliphatic monoepoxide.

Claim 36

A composition suitable for photocopolymerization comprising: (a) a cyclic vinyl ether containing compound, and (b) a vinyl cycloaliphatic monoepoxide.

Claim 37

A radiation cured coating derived from the composition of claim 1.